Kumman contrasts coding tools like Cursor and Windsurf, which help users create what they imagine, with AI features in familiar apps that can feel like extra work. In Gmail, a draft agent turns a short request about his sick daughter into a formal email that does not sound like him. The prompt is nearly as long as the draft.
How To Design Better AI Apps
Speaker
Pete Kumman, YC partner and Optimizely founder, discusses how to design AI apps with The Breakdown hosts at Y Combinator.
Kumman says generic system prompts can produce safe, one-size-fits-all results. He demonstrates that a prompt describing his role and preference for short emails produces a draft closer to his own style. He argues that users should be able to inspect and adjust these instructions.
Kumman uses the “horseless carriage” analogy for adding AI to existing software without redesigning it around AI’s capabilities. He compares this to early search engines that were digital directories and mobile apps that were websites in native wrappers. For email, he proposes an agent that can label, archive, and draft messages according to personal instructions.
Kumman describes AI models as capable assistants that need users to explain what work to do. He suggests agents could learn from past work and feedback, while users retain access to the instructions when they need to correct them. With tools connected across email, Slack, calendars, and documents, agents could handle repetitive workflows across apps.
Kumman advises founders to rethink existing tools from the ground up instead of simply inserting a chatbot. He says product teams should ask how AI can take repetitive work off users’ hands so they can focus on what matters.
Takeaways
- Test AI features against the time and effort they add, not just the quality of their output.
- Let users shape an agent’s instructions so its behavior fits their work and preferences.
- Use user feedback and past work to help agents learn, while keeping their instructions inspectable.
- Give agents tools to complete tasks across apps, rather than limiting them to chat responses.
- When redesigning a product for AI, start with the repetitive work users want to offload.
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What was claimed 9
- builtdeveloper and operator
“the integration the Gmail team built”
YouTube Verified2 sources· Talk, Web· archived
- role atPete Kumman is partner at
Y Combinator
“our partner here at YC”
YouTube Unverified1 source· Talk
- foundedPete Kumman founded Optimizely
“Pete was the founder of Optimizely”
YouTube Unverified1 source· Talk
- uses
“when I use tools like Cursor and Windsurf”
YouTube Unverified1 source· Talk
- usesPete Kumman uses
Cursor
“when I use tools like Cursor and Windsurf”
YouTube Unverified1 source· Talk
- feature
Gmail: AI drafts email from user instructions
“a little draft-writing agent that can create email drafts for me given some instructions”
YouTube Unverified1 source· Talk
- integrates with
“the integration the Gmail team built between their AI model, Gemini, and Gmail's interface”
YouTube Unverified1 source· Talk
- featureDen: Connects tools for knowledge work through MCP servers
“basically building Cursor for knowledge work”
YouTube Unverified1 source· Talk
- feature
ChatGPT: Brought chatbot AI to a mainstream audience
“ChatGPT brought it to the mainstream”
YouTube Unverified1 source· Talk









